BE537978A - - Google Patents

Info

Publication number

BE537978A

BE537978A BE537978DA BE537978A BE 537978 A BE537978 A BE 537978A BE 537978D A BE537978D A BE 537978DA BE 537978 A BE537978 A BE 537978A

Authority

BE

Belgium

Prior art keywords

anthraquinone

parts

mixture

diethyl

diethylcyclohexylamine

Prior art date

Links

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• 239000000203 mixture Substances 0.000 claims description 24
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 14
• CIXSDMKDSYXUMJ-UHFFFAOYSA-N n,n-diethylcyclohexanamine Chemical compound CCN(CC)C1CCCCC1 CIXSDMKDSYXUMJ-UHFFFAOYSA-N 0.000 claims description 13
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 12
• RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 10
• 238000000034 method Methods 0.000 claims description 10
• 239000000984 vat dye Substances 0.000 claims description 9
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
• 229910052802 copper Inorganic materials 0.000 claims description 8
• 239000010949 copper Substances 0.000 claims description 8
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 7
• 229910000881 Cu alloy Inorganic materials 0.000 claims description 6
• XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims description 6
• 150000003839 salts Chemical class 0.000 claims description 6
• PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 claims description 5
• 150000004056 anthraquinones Chemical class 0.000 claims description 5
• 239000000975 dye Substances 0.000 claims description 5
• 150000002148 esters Chemical class 0.000 claims description 5
• 239000002184 metal Substances 0.000 claims description 5
• 229910052751 metal Inorganic materials 0.000 claims description 5
• TVCIMZVAAUYMMM-UHFFFAOYSA-N n,n-diethyl-1-methylcyclohexan-1-amine Chemical compound CCN(CC)C1(C)CCCCC1 TVCIMZVAAUYMMM-UHFFFAOYSA-N 0.000 claims description 5
• KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 claims description 4
• 150000002739 metals Chemical class 0.000 claims description 4
• WITKIIIPSSFHST-UHFFFAOYSA-N 1-[(9,10-dioxoanthracen-1-yl)amino]anthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC1=C2C(=O)C3=CC=CC=C3C(=O)C2=CC=C1 WITKIIIPSSFHST-UHFFFAOYSA-N 0.000 claims description 2
• 229910052742 iron Inorganic materials 0.000 claims description 2
• PZNXLZZWWBSQQK-UHFFFAOYSA-N n-(5-benzamido-9,10-dioxoanthracen-1-yl)benzamide Chemical compound C=1C=CC=CC=1C(=O)NC(C=1C(=O)C2=CC=C3)=CC=CC=1C(=O)C2=C3NC(=O)C1=CC=CC=C1 PZNXLZZWWBSQQK-UHFFFAOYSA-N 0.000 claims description 2
• 238000002360 preparation method Methods 0.000 claims description 2
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 2
• 150000008064 anhydrides Chemical class 0.000 claims 1
• FFBHFFJDDLITSX-UHFFFAOYSA-N benzyl N-[2-hydroxy-4-(3-oxomorpholin-4-yl)phenyl]carbamate Chemical compound OC1=C(NC(=O)OCC2=CC=CC=C2)C=CC(=C1)N1CCOCC1=O FFBHFFJDDLITSX-UHFFFAOYSA-N 0.000 claims 1
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
• 239000000243 solution Substances 0.000 description 7
• 238000003756 stirring Methods 0.000 description 6
• 238000001816 cooling Methods 0.000 description 5
• 229910000029 sodium carbonate Inorganic materials 0.000 description 4
• AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 4
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
• 239000007864 aqueous solution Substances 0.000 description 3
• 238000004821 distillation Methods 0.000 description 3
• -1 ester salt Chemical class 0.000 description 3
• 239000011541 reaction mixture Substances 0.000 description 3
• NTSLROIKFLNUIJ-UHFFFAOYSA-N 5-Ethyl-2-methylpyridine Chemical compound CCC1=CC=C(C)N=C1 NTSLROIKFLNUIJ-UHFFFAOYSA-N 0.000 description 2
• 229910001369 Brass Inorganic materials 0.000 description 2
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
• MBQIBVUQWGJDCJ-UHFFFAOYSA-N N,N-diethyl-3-methylcyclohexan-1-amine Chemical compound C(C)N(C1CC(CCC1)C)CC MBQIBVUQWGJDCJ-UHFFFAOYSA-N 0.000 description 2
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
• 238000009835 boiling Methods 0.000 description 2
• 239000010951 brass Substances 0.000 description 2
• QZKRKMRVWWGTRU-UHFFFAOYSA-N 1,3-dichloro-2-methylanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=C(Cl)C(C)=C(Cl)C=C3C(=O)C2=C1 QZKRKMRVWWGTRU-UHFFFAOYSA-N 0.000 description 1
• RFKYAMWZNODXTH-UHFFFAOYSA-N 2-amino-1,5-dibenzoylanthracene-9,10-dione Chemical compound NC1=CC=C2C(=O)C3=C(C(=O)C=4C=CC=CC=4)C=CC=C3C(=O)C2=C1C(=O)C1=CC=CC=C1 RFKYAMWZNODXTH-UHFFFAOYSA-N 0.000 description 1
• CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical group [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 1
• 239000002253 acid Substances 0.000 description 1
• 229910045601 alloy Inorganic materials 0.000 description 1
• 239000000956 alloy Substances 0.000 description 1
• 230000008034 disappearance Effects 0.000 description 1
• 238000004090 dissolution Methods 0.000 description 1
• 230000032050 esterification Effects 0.000 description 1
• 238000005886 esterification reaction Methods 0.000 description 1
• 238000001914 filtration Methods 0.000 description 1
• MKQFOYWMVVVZHN-UHFFFAOYSA-N n,n-diethyl-4-methylcyclohexan-1-amine Chemical compound CCN(CC)C1CCC(C)CC1 MKQFOYWMVVVZHN-UHFFFAOYSA-N 0.000 description 1
• 230000000737 periodic effect Effects 0.000 description 1
• 239000000843 powder Substances 0.000 description 1
• 239000002244 precipitate Substances 0.000 description 1
• 239000000047 product Substances 0.000 description 1
• 238000005185 salting out Methods 0.000 description 1
• 239000011780 sodium chloride Substances 0.000 description 1
• 239000007787 solid Substances 0.000 description 1
• 239000000126 substance Substances 0.000 description 1
• 238000003828 vacuum filtration Methods 0.000 description 1